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Publication numberUS7298023 B2
Publication typeGrant
Application numberUS 10/492,922
PCT numberPCT/DE2002/003292
Publication date20 Nov 2007
Filing date5 Sep 2002
Priority date16 Oct 2001
Fee statusPaid
Also published asDE10151036A1, EP1436850A1, US20050048803, WO2003038921A1
Publication number10492922, 492922, PCT/2002/3292, PCT/DE/2/003292, PCT/DE/2/03292, PCT/DE/2002/003292, PCT/DE/2002/03292, PCT/DE2/003292, PCT/DE2/03292, PCT/DE2002/003292, PCT/DE2002/03292, PCT/DE2002003292, PCT/DE200203292, PCT/DE2003292, PCT/DE203292, US 7298023 B2, US 7298023B2, US-B2-7298023, US7298023 B2, US7298023B2
InventorsErwann Guillet, Peter Bonzani, Walter Fix, Henning Rost, Andreas Ullmann
Original AssigneePolyic Gmbh & Co. Kg
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Electronic device with organic insulator
US 7298023 B2
Abstract
The invention concerns an insulator for an organic electronic component, in particular, for an organic field-effect transistor (OFET) or for an organic capacitor. The insulating material is characterized in that it includes an almost constant relative dielectric constant, even in case of frequency variation in wide ranges, for example, between 1 Hz and 100 kHz.
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Claims(13)
1. In an electronic device comprising at least one of an organic field effect transistor or capacitor, which transistor and capacitor comprises an insulator layer and includes electrical and mechanical requirements and which insulating layer fulfills the electrical and mechanical requirements of the transistor or capacitor, the improvement comprising:
the insulating layer being at least partially based on organic material, and wherein the dielectric constant of the insulating layer remains substantially constant within a frequency range between 1 Hz and 100 Hz;
the insulator layer comprising a base polymer of PVDC-PAN-PMMA copolymer with the general formula

(—CH2Cl2—)x—(—CH2CH(CN)—)y—(CH2C(CH3)(CO2CH3)—)z,
wherein x, y, z, in each case, independently from one another, may assume values between 0 and 1.
2. In the device in accordance with claim 1, wherein the insulator layer comprises one of polyisobutylene and uncrosslinked EPDM (Ethylene Propylene Diene Monomer) as a base polymer.
3. In an electronic device comprising at least one of an organic field effect transistor or capacitor, which transistor and capacitor comprises an insulator layer and includes electrical and mechanical requirements and which insulating layer fulfills the electrical and mechanical requirements of the transistor or capacitor, the improvement comprising:
the insulating layer being at least partially based on organic material, and wherein the dielectric constant of the insulating layer remains substantially constant within a frequency range between 1 Hz and 100 Hz and wherein the insulator layer comprises a base polymer with the general formula

[Ax/B1−z],
wherein A is polyhydroxystyrene and B is poly(styrene-co-alyl-alcohol), polyvinylalcohol and/or poly-alpha-methylstyrene.
4. In an electronic device comprising at least one of an organic field effect transistor or capacitor, which transistor and capacitor comprises an insulator layer and includes electrical and mechanical requirements and which insulating layer fulfills the electrical and mechanical requirements of the transistor or capacitor, the improvement comprising:
the insulating layer being at least partially based on organic material, and wherein the dielectric constant of the insulating layer remains substantially constant within a frequency range between 1 Hz and 100 Hz and wherein the insulator layer comprises as a base polymer a compound of two polymers, with the general formula

[Az/By],
with A equals poly(vinyltoluene-co-alpha-methylstyrene) and B equals poly(styrene-co-allyl-alcohol), wherein the values of z and y may be equal or unequal and assume values between 0.5 and 1.
5. In an electronic device comprising an organic field effect transistor including an insulator layer and having electrical and mechanical requirements, which insulating layer fulfills the electrical and mechanical requirements of the transistor, the improvement comprising:
the insulating layer being at least partially based on organic material, and wherein the dielectric constant of the insulating layer remains substantially constant within a frequency range between 1 Hz and 100 Hz and wherein the insulator layer comprises as a base polymer a compound of two polymers, with the general formula

[Az/By],
with A equals poly(vinyltoluene-co-alpha-methylstyrene) and B equals poly(styrene-co-allyl-alcohol), wherein the values of z and y may be equal or unequal and assume values between 0.5 and 1.
6. In an electronic device comprising an organic capacitor including an insulator layer and having electrical and mechanical requirements, which insulating layer fulfills the electrical and mechanical requirements of the capacitor, the improvement comprising:
the insulating layer being at least partially based on organic material, and wherein the dielectric constant of the insulating layer remains substantially constant within a frequency range between 1 Hz and 100 Hz and wherein the insulator layer comprises as a base polymer a compound of two polymers, with the general formula

[Az/By],
with A equals poly(vinyltoluene-co-alpha-methylstyrene) and B equals poly(styrene-co-allyl-alcohol), wherein the values of z and y may be equal or unequal and assume values between 0.5 and 1.
7. In the electronic device of claim 1 wherein the insulator layer is structured.
8. In the device in accordance with claim 3 wherein the base polymer is a compound comprising 50% polyhydroxystyrene and 50% poly(styrene-co-allyl-alcohol).
9. In the device in accordance with claim 4, wherein the values of x and y are equal.
10. In the device, in accordance with one of the claims 8, 9, and 3-4 wherein the base polymer is dissolved in one of a polar solvent and a polar mixture comprising at least two solvents.
11. In the device of any one of claim 1 and 3-6 including an electronic circuit formed on a surface of said insulating layer and electrically operatively coupled to the transistor or capacitor.
12. In the device of claim 1 including an OFET circuit formed on a surface of said layer and electrically operatively coupled to at least one of the transistor or capacitor.
13. In the device of claim 1 including a transistor circuit formed on a surface of said layer.
Description

The invention concerns an insulator for an organic electronic component, in particular, for an organic field-effect transistor (OFET) and/or for an organic capacitor.

We know from C. J. Dury et al., Applied Physics Letters 73 1998, p. 108, that polyhydroxystyrene (PHS) is used as an insulator in OFETs. The main disadvantage of the material is that there is no known possibility thus far to structure the insulator economically. Loose ions inside the material represent an additional problem, which lead to an extremely low switching behavior. Moreover, PHS is relatively expensive.

Commercially available photosensitive resist (SC 100, Olin Hunt) was used as an insulator in a more recent publication (G. H. Gelinck et al, Applied Physics Letter 77 2000, p. 1,487). Due to the structuring of the photosensitive resist, the layers beneath suffer major corrosion or destruction, which is a substantial disadvantage of this method. This makes it practically impossible to use the insulator on already existing semiconductor layers such as, for example, polyalkylthiophene. However, the insulating layer above the semiconducting layer is deposited to produce the OFET, in which the source and/or drain electrodes are embedded. Damage to the already existing semiconducting layer cannot be tolerated during the manufacturing process.

Polyimide was also presented as insulating material (J. A. Rogers et al., IEEE Electron Devices Letters, Volume 21, Number 3, 2000, p. 100). Even when using the material, there is the fear of causing damage to the already finished OFET layers, since the material can only be processed at extremely high temperatures (˜400° C.). Since organic semiconductors or conductors can typically survive only significantly lower temperatures without damage (less than 200° C.), polyimide cannot be used in filly organic OFETs.

Independent of the processing characteristics of the familiar materials, an insulator, whose dielectric constant remained basically constant when the emitted frequency is changed, could not be found thus far. Rather, all these materials demonstrate a frequency-dependent change in the dielectric constant, which affects entire ranges.

Therefore, it is the challenge of the present invention to provide an insulator for a field-effect transistor, which at least partially consists of organic material and which overcomes the disadvantages of prior art.

The subject matter of the invention concerns an insulator for an organic electronic component, in particular, for an organic field-effect transistor and/or a capacitor, which is at least partially based on organic material, where the dielectric constant of the insulating layer essentially remains constant in a frequency range between 1 Hz and 100 kHz.

According to one embodiment, the insulator is comprised of polyisobutylene or uncrosslinked EPDM (Ethylene Propylene Diene Monomer) as base polymer (main component), which are only soluble in nonpolar hydrocarbons (hexane, heptane). The homogenous thickness of the layer that can be achieved with the material is between approx. 2 μm and 250 μm, whereby these layers still possess sufficiently high insulation characteristics. The material can be structured very easily, thus permitting hole contacts, which is another major advantage of the material (e.g. by means of lithography).

According to another embodiment, the insulating material is comprised of a commercially available PVDC-PAN-PMMA copolymer with the general formula
(—CH2Cl2—)x—(CH2CH(CN)—)y—(—CH2C(CH3)(CO2CH3)—)z,
wherein x, y, z, in each case, independently from one another, may assume values between 0 and 1, preferably values as indicated in the examples.

The PVDC PAN PMMA copolymer is preferably used in combination with HMMM (hexamethoxy methal melamine) and/or Cymel crosslink components, whose ratio can be varied widely (dissolved in dioxane). The material also permits very simple structuring without being crosslinked yet at the same time. The material can be crosslinked at very low temperatures (approx. 70° C.) and becomes then resistant to all subsequent steps that are necessary to complete an OFET and to put together an integrated circuit.

According to one embodiment, the insulating compound comprised of a base polymer with the general formula
[AX/B1−z],
is used, wherein A, for example, is polyhydroxystyrene and B is poly(styrene-co-allyl-alcohol) such as, for example, polyvinyltoluol, poly(alpha-methylstyrene).

In particular, compounds such as, for example, [50% polyhydroxystyrene/50% poly(styrene-coallyl-alcohol)], dissolved in polar solvents such as, for example, dioxane, are preferred in this regard. A major advantage of the material is that a layer can be deposited on P3AT with very little damage.

Finally, according to another embodiment, an insulator is used comprising a compound of two copolymers, with the general formula
[Az/By],
wherein, in particular, a compound of poly(vinyltoluene-co-alpha-methylstyrene)/poly(styrene-co-allyl-alcohol) is suitable. The x and y indices may thereby be equal or unequal and assume values between 0.5 and 1. There is a particular preference for x and y to be equal. Again, the compound is preferably dissolved in polar solvents, in particular, dioxane.

Surprisingly, the materials mentioned fulfill characteristic profiles allowing their use, in particular, as insulating layer in OFETs. This is particularly so, since an insulating layer made up of one or a compound of several mentioned materials fulfills the following process, electrical and mechanical requirements and, at the same time, is a very inexpensive material system.

Process requirements:

    • The insulating layer easily dissolves in conventional organic solvents such as, for example, dioxane, butanol and other alcohols, etc.
    • Depositing the insulating layer onto already existing OFET layers (e.g. semiconductor layer) does not damage these layers, either through corrosion or etching, nor does it change their characteristics.
    • After depositing, the insulating layer can be structured. Also, structuring does not negatively affect existing layers. Structuring is absolutely necessary in order to create integrated circuits, which consist of several OFETs, since structuring is required to make link circuits between the gate electrode of one OFET and the source or drain electrode of another OFET possible.
    • After structuring, the insulating layer is chemically and thermally stabile vis-à-vis the process steps that are required to deposit and structure subsequent OFET layers (e.g. gate electrode).

b) Electrical requirements:

    • The relative dielectric constant of the insulating layer is nearly constant in a frequency range between 1 Hz and 100 kHz. The relative dielectric constant is considered “nearly constant” in this context, if it varies by 50% or less.
    • Preferably, the relative dielectric constant of the insulating layer has at least a value of about 2 for the mentioned systems, thus allowing OFETs to be produced that work at low voltage.
    • It is advantageous that leakage currents through the insulating layer, even in the case of very thin layers, are negligibly small vis-à-vis the source-drain current, i.e. they preferably lie belowl nA (depending on the OFET geometry).
    • The dielectric strength of the insulating layer is high and has a preferred value of at least 5*105 V/cm.
      Preferably, the insulating material should not contain any movable impurities (e.g. ions).
    • Preferably, the threshold voltage of the OFET is not displaced by the insulating system.
      Mechanical requirements:
    • To a certain extent, the insulating layer is resistant against mechanical force such as bending, stretching or compressing.
    • Depositing the insulating layer by spin-coating, doctoring, printing or spraying is done in such a way as to create a plane-parallel, even, homogeneous layer free of defects.

To produce a complete OFET, structurable layers of either photosensitive resist or metal are deposited on the insulating layer. After structuring, the insulating layer can be precisely removed with suitable solvents and thus structured as well. This way, the insulating layer is always structured at temperatures below 100° C. so that processing in this way has no negative effect on already existing functional layers (e.g. semiconductors).

The excellent electrical characteristics, i.e., high dielectric constant, high breakdown voltage and low leakage currents of the material systems under consideration continue to permit the production of relatively thin insulating layers, which leads to a drastic reduction of the required gate voltage to preferred values below 10 V.

In this context, the term “organic material” or “organic functional polymer” comprises all kinds of organic, metal-organic and/or organic-inorganic synthetic materials (hybrids), particularly those, which are referred to, for example, in the English language, as “plastics.” This concerns all types of materials with the exception of semiconductors, which form classic diodes (germanium, silicon), and the typical metallic conductors. Thus, dogmatically speaking, there are no plans of limiting the use to organic, that is, carbon-containing materials, rather, the wide use of, for example, silicon is also considered. Moreover, the term should not be subject to any limitations with regard to molecular size, in particular, limitations to polymer and/or oligomer materials, rather the use of “small molecules” is also quite possible. The word component “polymer” within functional polymer is historic and insofar contains no information about the existence of actual polymer compounds.

Following, the invention will be explained on the basis of some examples, which describe embodiments of the invention:

EXAMPLE I Use of Polyisobutylene (PIB) as an Insulator

0.4 g of PIB (Aldrich) was dissolved in 9.6 g of hexane at room temperature;

the solution was filtered through a PTFE 0.45 μm syringe filter;

the solution was then spin-coated onto the substrate (4,000 rpm for 20 seconds), which was already fit with source/drain electrodes and semiconductors (top-gate design). The result was a very homogenous layer, approx. 260 nm thick;

the sample was dried under a dynamic vacuum for approx. 30 minutes at room temperature;

then a thick layer of photosensitive resist was deposited on the insulator, exposed and developed under normal circumstances;

the sample was immersed in a hexane bath and the insulator was stripped in the areas that were free of resist;

the remaining resist was removed with a suitable solvent;

EXAMPLE 2 Use of PVDC-PAN-PMMA (x=0.89, y=0.03, z=0.08) as Insulator

0.4 g of PVDC-co-PAN-co-PMMA (Aldrich) was dissolved in 9 g of dioxane at 40-50° C.

0.5 g of cymel 327 (Cytec Industries, Inc.) and 0.1 g of campher sulfonic acid were then added and stirred for a few seconds;

the solution was filtered through a PTFE 0.45 μm syringe filter;

the solution was spin-coated onto the substrate (8,000 rpm for 20 seconds), which was already fit with source/drain electrodes and semiconductors (top-gate design). The result was a very homogenous layer, approx. 400 nm thick;

the sample was dried under a dynamic vacuum for approx. 30 minutes at room temperature;

the layer was vacuum-coated with a thin gold layer, which in turn was structured by means of photolithography (photosensitive resistant, then etched with a potassium carbonate solution);

the deposited metal mask allows structuring of the insulating layer in that the now freed insulating surfaces can be removed with a toluene-soaked rag;

the remaining gold residue was removed with a potassium carbonate solution

the last step was to crosslink the insulator (10 minutes at 90° C.).

EXAMPLE 3

Use of [50% polyhydroxystyrene/50% poly(styrene-co-allyl-alcohol) as insulator. The polymer compound was then dissolved with dioxane and filtered with a 0.2 μm filter. Then, the insulating layer was then pre-baked on the hot plate at 100° C. for 30 minutes. As in example 2, structuring is also carried out by means of “metal masks.”

The insulating material according to the invention shows no substantial frequency-dependent variation of the dielectric constant. Either the orientation of existing anisotropic molecules or a lack of mobile charge carriers as well as mobile ions may be responsible for this phenomenon. At any rate, no significant variation of the dielectric constant, exceeding approx. 50%, could be established within a frequency range of almost 100 kHz.

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Classifications
U.S. Classification257/642, 257/632, 257/E21.259
International ClassificationC08L101/12, H01L21/822, H01L51/30, C08L23/00, C08K5/06, C09D5/25, C08L25/00, H01B3/44, H01L29/786, H01B3/28, H01L21/312, H01L51/05, H01L27/04, H01L23/58, C08L29/04, H01G4/18, C08L27/08, H01L21/47
Cooperative ClassificationH01L21/312, H01L51/052, H01B3/447, H01B3/442, H01G4/18
European ClassificationH01B3/44C, H01L51/05B2B2B, H01G4/18, H01B3/44F
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